Ever since his first appearance back in 1963, Norman Osborn, aka Green Goblin, has acted as Spider-Manโs archnemesis and one of the most fearsome villains in Marvel Comics history. However, that all changed when, in 2020, Norman literally had all his sins removed from his body by the Sin-Eater. Since then, the former supervillain has been trying to redeem himself by becoming an ally to Spider-Man. As of now, Norman has even taken on the Spider-Man mantle while Peter is off on an intergalactic mission. Still, no matter how many people Norman saves, he can never wash off the horrific crimes heโs committed as the CEO of Oscorp, the Iron Patriot, and, of course, the Green Goblin.
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For most of Marvelโs history, Norman Osborn has dedicated his life to destroying Peter and everyone he loves out of pure spite. Before his transformation in 2020, even when Norman wasnโt wearing his iconic Green Goblin costume, he was still committing countless atrocities that have cost many people their lives. These are the worst deeds Norman has ever committed in Marvel Comics.
7) Faking Aunt Mayโs Death

When Peter lost Aunt May to a stroke, he was devastated by the loss of his surrogate mother. However, the event was Norman’s plot to make Peter suffer. Norman had kidnapped the real Aunt May, and the person who died in front of Peter was an actress Norman killed. Even worse, when Peter discovered the truth, he also found out that Norman had put a device in the back of Mayโs head that was slowly killing her. Unfortunatley, if the device were removed, it would trigger the detonation of bombs across the world that would turn millions of people into goblin-like creatures. Luckily, Peter managed to save May and have the device safely removed. Nonetheless, it was still one of the worst cases of psychological torture Peter ever experienced.
6) Killing Ben Reilly

Norman was the mastermind behind the controversial Clone Saga, where a clone named Ben Reilly believed himself to be the real Peter Parker. All of this left the original Peter in a maddening identity crisis as he began to think he was the clone. Peter and Ben would eventually put their conflict aside to fight various villains sent by Norman. In one final act, Norman launched his glider at Peter, but Ben jumped in the way and got impaled. As Ben died in Peterโs arms, he turned into dust. Although his death proved that Ben was the clone all along, Peter still lost a person he had begun to see as a friend.
5) Killing Flash Thompson

Flash Thompson is well-known for evolving from Peterโs high school bully to one of his closest friends. Flash would also become a major crime-fighter when he merges with the Anti-Venom Symbiote to become Agent Anti-Venom. However, Flash wasnโt the only one who obtained a Symbiote. To become stronger, Norman merged with the homicidal Carnage Symbiote, transforming into the Red Goblin. When Flash thwarted Normanโs plans to kill MJ and Aunt May, the enraged villain murdered him instead. Peter was heartbroken to bury yet another close friend. Although Flash would eventually return, Normanโs act was still a cruel expression of Normanโs spite.
4) Selling His Sonโs Soul to Mephisto

Norman Osborn has never been a good father to Harry, but selling his sonโs soul to Mephisto, the ruler of Hell, for financial gain is just ridiculous. When Norman was a failing businessman drowning in debt, he sold Harryโs soul to Mephisto so that Oscorp could become the massive corporation that it is today. Not only did this deal condemn Harryโs soul to Hell, but itโs also heavily implied that everything bad that ever happened to Harry stems from Mephistoโs machinations and the deal the demon made with Norman. This includes Harryโs drug addiction, Gwen Stacyโs death, his insanity-induced transformation into the second Green Goblin, and his eventual death. Normanโs greed cost him the life and soul of his only son.
3) Kidnapping May Parker

In one of the most tragic moments in Spider-Man history, Peter and MJ are getting ready to welcome their daughter, May Parker, to the world. However, MJ suffers from complications when she goes into labor, and May doesnโt make it. As Peter and MJ grieve the loss of their daughter, things take an even darker turn. Itโs revealed that one of the nurses, secretly working for Norman, abducted May while she was still alive. Mayโs ultimate fate is never revealed, and for all we know, Norman could have killed her himself. Of course, whether she was dead or alive became moot when โOne More Dayโ retconned Peter and MJโs entire relationship and Mayโs existence.
2) Killing Gwen Stacy

In one of the most shocking acts in comic book history, Norman murdered Peterโs longtime girlfriend, Gwen Stacy, after kidnapping her and holding her hostage over the Brooklyn Bridge. When Peter arrived to save her, Norman dropped Gwen. As Gwen plummeted to her death, Peter dove after her and managed to catch her with his webbing. However, the whiplash from the fall made Gwen snap her neck, killing her instantly. As Peter held Gwen in his arms, he swore to kill Norman for taking away the person he loved most in the world. Gwen Stacyโs murder remains the most infamous action Norman ever committed, with its impact still felt by both Peter and readers decades later.
1) Invading Asgard

When Norman killed the Skrull Queen during Secret Invasion, he became the new head of S.H.I.E.L.D., which he renamed H.A.M.M.E.R. During this time, Norman took on the identity of Iron Patriot, forming the Dark Avengers and the Cabal. However, things worsened when Asgard arrived on Earth. Norman viewed Asgardโs presence as an act of war. To justify an invasion, Norman orchestrated the deaths of thousands of people to frame the Asgardian Volstagg for the massacre. Using the chaos as justification, Norman unleashed the full force of H.A.M.M.E.R. and the Dark Avengers to invade Asgard. When the Avengers arrived to stop the conflict, Norman commanded the corrupted Sentry to destroy Asgard. Normanโs actions claimed countless lives and inadvertently released Sentryโs genocidal Void split personality, which threatened to wipe out humanity.
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